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Effect of molecular oxygen on the kinetics and mechanism of the reaction of 2-bromo-1-ethylpyridinium bromide with triethylamine in acetonitrile

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Theoretical and Experimental Chemistry Aims and scope

The nucleophilic aromatic substitution of bromine into 2-bromo-1-ethylpyridinium bromide (I) in its reaction with triethylamine (II) is accompanied by subsequent oxidation of the intermediates by molecular oxygen dissolved in acetonitrile. The following reaction products were identified: 1-ethyl-2-pyridone, triethylamine N-oxide, and the hydrobromide salt of triethylamine. The reaction kinetics was studied with reagents ratios

[II] >> [O2] >> [I]. The reaction has first-order kinetics relative to the reagents.

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References

  1. G. P. Klimisha, I. P. Krainov, E. G. Protsenko, et al., Khim. Geterotsikl. Soedin., No. 2, 264 (1979).

  2. S. G. Sheiko, E. S. Mitchenko, and G. D. Titskii, Ukr. Khim. Zh., 52, No. 9, 988-990 (1986).

    CAS  Google Scholar 

  3. G. D. Titskii and T. S. Gaidash, Teor. Éksp. Khim., 41, No. 4, 242-246 (2005). [Theor. Exp. Chem., 41, No. 4, 253-258 (2005) (Engl. Transl.).]

    Google Scholar 

  4. T. M. Ivanova and S. M. Shein, Zh. Org. Khim., 15, No. 2, 348-356 (1979).

    CAS  Google Scholar 

  5. S. M. Shein, Izv. Sib. Otdel. Akad. Nauk SSSR, Ser. Khim., No. 4, 74-83 (1990).

  6. L. Grossi and S. Strazzari, J. Chem. Soc., Perkin Trans. II, No. 10, 2141-2146 (1999).

  7. V. N. Knyazev and V. N. Drozd, Zh. Org. Khim., 31, No. 1, 3-30 (1995).

    CAS  Google Scholar 

  8. I. B. Afanas’ev, Usp. Khim., 48, No. 6, 976-1014 (1979).

    Google Scholar 

  9. A. A. Serdyuk, M. G. Kasyanchuk, and I. A. Opeida, Zh. Fiz. Khim., 84, No. 3, 456-459 (2010).

    Google Scholar 

  10. G. D. Titsky, T. S. Gaidash, and E. S. Mitchenko, Abstracts of the Fifth International Conference “Chemistry of Nitrogen-Containing Heterocycles (CNCH2009),” Kharkiv, October 5-9, 2009, Kharkiv (2009), p. 58.

  11. G. D. Titskii and T. S. Gaidash, Teor. Éksp. Khim., 34, No. 5, 286-289 (1998). [Theor. Exp. Chem., 34, No. 5, 261-264 (1998) (Engl. Transl.).]

    Google Scholar 

  12. G. D. Titskii and E. S. Mitchenko, Zh. Org. Khim., 24, No. 10, 2161-2166 (1988).

    CAS  Google Scholar 

  13. L. M. Litvinenko, G. D. Titskii, and E. S. Mitchenko, Zh. Org. Khim., 19, No. 9, 1970-1975 (1983).

    CAS  Google Scholar 

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Authors and Affiliations

  1. L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, Vul. R. Luxemburg, 70, Donets’k, 83114, Ukraine

    G. D. Titskii, E. S. Mitchenko & T. S. Gaidash

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  1. G. D. Titskii
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  2. E. S. Mitchenko
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  3. T. S. Gaidash
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Correspondence to G. D. Titskii.

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Translated from Teoreticheskaya i Éksperimental’naya Khimiya, Vol. 46, No. 4, pp. 230-233, July-August, 2010.

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Titskii, G.D., Mitchenko, E.S. & Gaidash, T.S. Effect of molecular oxygen on the kinetics and mechanism of the reaction of 2-bromo-1-ethylpyridinium bromide with triethylamine in acetonitrile. Theor Exp Chem 46, 239–242 (2010). https://doi.org/10.1007/s11237-010-9146-x

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